SYNTHESIS OF DERIVATIVES OF 1,2-DICHLORO-4-BENZENESULFONAMIDO-5-NITROBENZENE AND THEIR USE IN THE CHEMOTHERAPY OF SPONTANEOUS CANCERS

doi:10.1139/V65-196

Paper

SYNTHESIS OF DERIVATIVES OF 1,2-DICHLORO-4-BENZENESULFONAMIDO-5-NITROBENZENE AND THEIR USE IN THE CHEMOTHERAPY OF SPONTANEOUS CANCERS

Published May 1, 1965 · D. Woolley, T. V. D. Hoeven

Canadian Journal of Chemistry

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Abstract

A series of compounds related to 1,2-dichloro-4-benzenesulfonamido-5-nitrobenzene has been synthesized. These included derivatives in which ionizable groups had been placed in the para position of the benzenesulfonamido portion to confer on the compounds water solubility at physiological pH. Thus, carboxyl and quaternary ammonium groupings were introduced in this position. Water solubility was also conferred by introduction at the same position of non-ionizable groups such as polyhydroxyalkylamido groups. Additional relatives of the parent compound in which the chlorine atoms were replaced by methyl groups, and in which para-substituted benzenesulfonamido groups replaced those in the 4 and 5 positions, were synthesized. These compounds were tested for their ability to cure permanently the spontaneous mammary cancers of two strains of mice. All compounds were tested in combination with 1,2-dimethyl-4-(p-carboxyphenylazo)-5-hydroxybenzene. The most active substance found was 1,2-dichloro-4-(p-carboxybenzene...

In Vitro Study

Study Snapshot

1,2-dichloro-4-benzenesulfonamido-5-nitrobenzene derivatives show potential in chemotherapeutic treatment of spontaneous mammary cancers, with 1,2-dichloro-4-(p-carboxybenzene) being the most active substance.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

SYNTHESIS OF DERIVATIVES OF 1,2-DICHLORO-4-BENZENESULFONAMIDO-5-NITROBENZENE AND THEIR USE IN THE CHEMOTHERAPY OF SPONTANEOUS CANCERS

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References

A FURTHER STUDY OF THE APPARENT SYNTHESIS OF VITAMIN B(12) BY MAMMARY CANCERS OF MICE.

Mice with mammary cancers can synthesize vitamin B12, potentially benefiting the development of targeted cancer drugs without harming the host animal.

SELECTIVE TOXICITY OF 1,2-DICHLORO-4,5-DIAMINOBENZENE: ITS RELATION TO REQUIREMENTS FOR RIBOFLAVIN AND VITAMIN B12

1,2-dichloro-4,5-diaminobenzene is toxic to species without a nutritional need for riboflavin and vitamin B12, but not to those with a need for both vitamins, suggesting that properly constructed analogs of essential vitamins may circumvent this counteraction.

Inhibition of Synthesis of Vitamin B12 and of Riboflavin by 1,2-Dichloro-4, 5-diaminobenzene in Bacterial Cultures

1,2-dichloro-4,5-diaminobenzene inhibits vitamin B12 and riboflavin synthesis in Bacillus megatherium, potentially causing selective toxicity by inhibiting biosynthetic processes in vitamin formation.

Citations

Preparation and antitumor activity of some Schiff Bases of 2'-amino-4',5'-dichlorobenzenesulfonanilide and 2'-amino-p-toluenesulfonanilide.

The Schiff bases of 2'-amino-4',5'-dichlorobenzenesulfonanilide and 2'-amino-p-toluenesulfonanilide showed no significant antitumor activity against L-1210 leukemia.